Stiles is a Cherry Popping King
by onlymystory
Summary: SwingSetinDecember posted this on tumblr: seeing how dylan is everyone's first. there should be a fic where stiles is everyone's first but no one's last UNTIL DEREK WHO WANTS TO BE WITH STILES FOREVER Then this happened. (All the main pack are involved but FF only allows me to list 4 characters. So yeah).
1. Chapter 1

**This was based on a tumblr prompt. The primary couple of the story is Stiles/Derek. The last (and long) chapter will be Stiles/Derek. But the rest of the pack is what you're reading now.**

* * *

It's not really a thing the pack talks about.

In fact, Stiles really isn't sure how it happened in the first place.

There's a possibility the problem is in his word choice. Like when he said he wanted to do it many times, in many different positions, Stiles wasn't trying to imply that he'd never done it. Or when he asked Danny if gay guys found him attractive, he was mostly conducting a research experiment in his head.

By it, he means sex. Clarity seems to be important lately.

Actually, as it turns out, he's managed to somehow become a sort of sex guru of the pack. Sex expert. Sexpert. Oh god, Stiles, turn off your brain.

Unfortunately, Stiles is apparently only the pack's go to the first time around. That's right folks, Stiles Stilinski is Beacon Hills' own cherry popping king. Emperor Deflowerer. No seriously did Derek mash up his entire Adderall prescription into tonight's pizza because Stiles' brain needs to stop this.

Somehow though, as he sits outside with Derek after a pack barbecue celebrating Lydia's return home—she finished what should have been 6 years of grad school in 4 years, to no one's surprise, especially since she started undergrad as a junior—Stiles is realizing that he managed to be everyone's first. Derek is busy talking to Boyd on his other side, derailing their previous conversation about whether Derek should open a diner like his mom always wanted to, so Stiles figures he has some time to reflect on how such a thing came to pass.

* * *

**SCOTT: 7****th**** grade.**

"Hey Stiles?" Scott raises his head from the foot of the bed where he was digging underneath for the dirty magazine Stiles said he hid under it.

"Yeah buddy." Stiles debates Cheetos vs Fritos. On the one hand dip, on the other awesome cheese dust lickage potential.

"How come you have magazines with naked guys and girls?"

Stiles doesn't hear any judgment in Scott's voice, just curiosity. "Because I like both."

"Do you like one more than the other?"

"Depends on the day."

Scott huffs. "Huh."

Stiles pushes the chips aside momentarily. This has now taken at least five minutes of Scott's concentration, which as his best friend he knows means they're supposed to talk about it. "You can borrow the one with the guys if you want," he offers generously. His mom is always telling him that people can like whoever they want but his dad likes to remind him that not everyone is ready to talk about it.

Scott shakes his head. "I looked a little. I don't think I really like guys like that. But I…"

"But what?" Stiles flops forward so his head is down at Scott's end of the bed.

"Well maybe I'm one of those people who doesn't know what he likes until he tries it," says Scott. "Like maybe I would like sex with a guy."

Stiles thinks for a minute. "We could try it."

"What? No. We don't know where things go or…"

"No!" Stiles is quick to cut him off. "Not like sex sex. Ew. But like hand jobs. I mean we do it to ourselves, right? It can't be that different with another person."

Scott agrees surprisingly easily to Stiles' various arguments for mutual hand jobs. But then Stiles always did make really good arguments.

"So um, how should we do this?" asks Scott.

"Maybe pillows?" suggests Stiles. They shuffle up to the top of the bed and push the covers down—Stiles also hops up to lock the door—and lay back like they're going to sleep. "I don't think this will work. I mean, it works if it's just me, but…"

"Yeah. Scott turns to his side. "Like this."

Stiles shifts and nods. "Yeah that's not bad." Okay now it's kind of awkward. They both stare at each other for a while and then Scott squirms out of his boxers and Stiles follows his lead.

"Are we supposed to look?" Scott's eyes are firmly on Stiles' forehead.

"We don't have to look a lot."

This seems to be a decent arrangement, though after getting enough of a gander for a comparison chart (not that Stiles would actually make one), he stares pretty steadily at Scott's collarbone, while Scott seems to be analyzing his left shoulder.

They have a lot of false starts—it turns out Scott has to get himself at least halfway hard before he really starts responding to Stiles' touch, though he tells Stiles that it's probably the situation and not that Stiles is bad at this.

After a few winces and muttered "ow!s", Stiles remembers the lotion in his nightstand.

Things go better after that. Stiles comes first. He's working on a theory that his heart is picky but his dick is easy. Obviously that will need more research.

Scott's quiet and reserved when he comes and Stiles thinks it's cute the way Scott's eyes flicker brightly, like they're smiling, when it happens.

"So?" asks Stiles, once they can breathe normal again and he's semi-wiped his hand off on the sheets.

Scott thinks. "I still just like girls. But that was nice. Thanks."

Stiles nods. He's going to count it as a successful experiment anyway.

They change the sheets and turn the TV on to old Doctor Who episodes and if Stiles remembers in the future that at least in one way, he's the more blessed of the two of them, at least he never tells Allison.

* * *

**Notes: I like to think Stiles considers everything to be research or an experiment. For science. He probably likes Science Bros too.  
Stiles went with Cheetos.  
****_Next time…Jackson gives his first blow job. Stiles gives it an 8.3 on execution but full marks for enthusiasm._**


	2. Chapter 2

Derek pokes Stiles. He nearly flails out of his chair in response. Some things couldn't be changed by grad school.

"Yeah?"

"Curly fry for your thoughts?"

Stiles accepts happily. The fry is still warm too. "Just thinking about an old memory."

"Good one?" Derek asks easily enough but there's still a cautious tone underneath. They've both gotten better over the years at moving on from the loss of family—in large part because of each other—but there can still be moments when memories hit out of the blue.

"You could say that," grins Stiles.

"No private conversations!" yells Erica from across the 'you tried' version of a circle they've created.

"There's no such thing around you people!" Stiles yells back at her and throws a carrot off Derek's plate at her. He's not going to waste the fries.

Boyd leans over Derek and steals a couple fries. It's like he doesn't think Stiles won't get revenge for that later. "What were you thinking about anyway? You were pretty zoned out."

Stiles figures if they're going to keep pestering him, he'll let them live with the mental image. "My first hand job."

Derek is not alone in giving Stiles an odd look. Though admittedly Stiles is pretty sure Derek's the only one actually staring at Stiles' hands. He mentally catalogues it in his things-I-notice-about-Derek-Hale-and-will-remember -in-anticipation-of-the-day-he-figures-out-what-he -wants file.

Lydia halfway curls away from Isaac to pay attention to the conversation. "Who was it?"

"Me!" answers Scott proudly, before Stiles can say anything. "Wait, right? It was me?"

Stiles coughs through his laughter—Erica isn't even bothering to hide hers—and nods. "Yeah Scott, you were still one of my firsts."

"One?" asks Allison, quirking an eyebrow at him.

"Well there's hand jobs, & blow jobs, & then like actual sex, and then there's first time with a guy or a girl." Stiles shrugs. He had a list. Pretty much everything got checked off by the end of sophomore year. Okay so there are still a few things he wants to try but he's holding those back for the right alpha guy. GUY. Geez brain, wake up.

Erica drags her chair away from Scott and Allison and back to Boyd so she's closer to the conversation. It doesn't escape Stiles' notice that everyone else does the same. "So who was your first blow job?"

Stiles takes the beer Derek offers him (Derek, who is still looking more closely at certain parts of Stiles' anatomy than reacting to the conversation) and takes a long pull before answering. "A gentleman doesn't suck and tell."

"Because you're a gentleman," snickers Isaac.

Stiles shakes his head.

"Oh just tell them!" yells Danny, briefly raising his head up from where he was napping on Jackson's legs. "They'll never let it go, otherwise."

"Fine," huffs Stiles. "The first blow job I ever gave was to Danny."

A chorus of shock and disbelieving shouts greet that announcement. The one from Danny of course registers loudest. "I think I'd remember if you gave me my first blow job," says Danny." My first was during a game of 7 Minutes in Heaven at Lydia's eighth grade graduation party."

"Yeah," says Stiles. "And you kept sneaking extra shots with Jackson and then he started flirting with Lydia and you got pissed off and insisted everyone play 7 Minutes in Heaven. You drew my name."

Danny moans and drops his head in his hands. "Oh my god, I lost part of my virginity to Stiles fucking Stilinski."

"Hey!" snaps Stiles indignantly. "I gave you a damn good blow job!"

"I don't understand anything," mutters Scott.

"That's the problem," moans Danny. "I modeled my technique after that night. Do you know how many rave reviews I've gotten over my sucking abilities?! And now I learn it's—oh god—a Stilinski special."

Stiles, Derek, and Lydia all burst into laughter at that one.

Danny's face pales all of a sudden and he squeaks. "Oh fuck."

Jackson cringes, enough that even Stiles picks up on it. Danny turns and stares at Jackson. "We have the same technique. I never really thought that much about it but we have the exact same tricks."

Stiles leers at both of them. It's that or choke to death on his own laughter induced tears.

Isaac is hunched over Lydia, he's laughing so hard. "Are you…telling us…that Stiles took Jackson's cock sucking virginity too?"

Jackson growls at him. "Shut up, Lahey."

"I need to hear this story," demands Erica. She's echoed by Allison and Lydia. Since no one, not even Derek and especially not Jackson tonight, has ever won an argument against the trio, Stiles leans back in his chair and begins. "It was a late summer night, a few weeks before freshman year of high school…"

* * *

"Stilinski!" Tap tap tap. "Stilinski!"

Stiles registers—finally—that the tapping is not an elf knocking on his brain (it's almost Christmas…in 6 months…whatever, don't judge) but someone at his window that keeps hissing his name and throwing pebbles.

He'd hope for Lydia (or this guy Eli who transferred into the last month of 8th grade) but that's really not his luck. Of course, he didn't really expect who was there either. "Jackson?! What the fuck are you Romeoing my window for?"

Jackson glares. "You can't just turn nouns into verbs, Stilinski."

"If Buffy can do it, I can do it. What. Do. You. Want?"

Jackson sighs, sounding terribly annoyed. "I need your help."

"With?" Geez, Stiles is fine being a good Samaritan if he has too but not if he has to pull teeth.

"Can I come inside first?"

"Fine. Hang on." Stiles lets Jackson in the front door—windows are currently just a he and Scott thing. "My dad's on a late shift tonight so they don't actually have to be quiet. So what's the deal?" asks Stiles once they're back in his bedroom.

Jackson shuffles his feet and word vomits at him. "I need to know how to give a blow job and Greenberg said that Owen said that you went to an upperclassman party and blew a senior and he won't stop talking about it so I thought maybe you could teach me."

"Why?"

"Can't you just say yes or no?"

"No. Because my answer depends on why you need my help. So…why do you need to know?"

Jackson huffs. "I want to ask Danny out."

"I didn't realize Danny required a first date to go quite that far." Stiles tries to say it as nicely as possible because one, it's really sad if Jackson thinks sex is the only way to get Danny and two, it's even more fucked up if that's true.

"He doesn't," assures Jackson. "But we've been friends forever. If he said yes and it did go there. I don't want to fuck this up."

"So why me?"

"Because we keep each other's secrets," says Jackson in a low voice.

Stiles was already leaning towards saying yes, he might be only 15, but he's figured out he likes what sex he's had. But that convinces him that this isn't some trick from Jackson.

They don't get along much. Never have, never will. Up until the last couple years they had the same social circle, but as always things change. To most of their classmates, Stiles & Jackson are at best, coldly polite acquaintances. But Stiles is the one who made peanut butter and potato chip sandwiches for the kid crying in his front yard in second grade, the day Jackson found out he was adopted. Stiles never really understood why it bothered Jackson so much, but he figured his opinion wasn't the point. Jackson refused to tell anyone else until 3 years later. And Stiles kept his secret.

And right now, Jackson's the one who was at the hospital six weeks ago getting stitches. He knows Sheriff Stilinski isn't working a late shift. He knows there's a bed and a hand that can't quite grip like it used to and a smile that takes more effort than these things should. Even Scott doesn't know that secret yet.

So sure, in public they hate each other. But in private…they're far more alike than most people know.

"I'm not blowing you," says Stiles. "You'll just end up focusing on coming and forget to pay attention. If you want to learn, you're sucking me off."

Jackson shrugs. "Yeah okay."

They both shuffle out of their jeans and Stiles sits on the edge of his bed in his boxers. Jackson kneels in front of him. "I know not to use my teeth."

Stiles laughs and it helps the weird tension in the room. "Start slow."

"Do I just…like pull you out?"

"You can. Or I can. Part of good sex is responding to the moment and not overthinking it."

Jackson runs his knuckles over the outline of Stiles' cock as he speaks. Stiles can feel the blood rush as he gets a little bit harder. Jackson gently tugs him out and strokes. "Is this okay? I feel like I need a warmup."

Stiles tries to nod reassuringly. Jesus, Jackson's a natural. "'S fine. When you're ready, start light. Like kiss the tip or lick a little. If you tease it out more, the feel of your mouth will take Danny's breath away."

Jackson settles in at Stiles' feet and concentrates. After a few minutes, he slips one hand down to cup Stiles' balls and keeps stroking with the other. He tastes hesitantly, with cautious licks, and Stiles shoves a fist in his mouth to bite back a moan. Jackson leans in and swipes his tongue in broad strokes across the head of Stiles' dick.

"Good?" He asks, looking up at Stiles, his eyes dark.

"Perfect," manages Stiles. How did he not know how beautiful Jackson could be?

Jackson presses a kiss right on the tip and before Stiles can decide if begging Jackson for more is a terrible idea, Jackson's swallowing him down.

Stiles fists his hands in the sheets to keep himself from bucking up into Jackson's mouth. But he wants. Oh god does he want.

Like everything else that Jackson Whittemore decides to do, he's a quick learner here too. Jackson's tongue moves in little flicks against Stiles' cock as he moves up and down. He can't take Stiles in too far, but it's more than enough.

"Jacks," whimpers Stiles. "You gotta pull back. I'm gonna come."

Jackson keeps his mouth wrapped around Stiles' dick, looks up at him and nods for Stiles to go ahead.

Stiles comes with a shudder and a muffled cry. When he recovers enough to process, Jackson has a soft smile as he licks his lips. Stiles tugs Jackson up to him and kisses him while he strokes Jackson's dick. He's quick and efficient and they're still teenagers so it's only a few more seconds before Jackson's coming too.

They clean up sometime later. Stiles offers Jackson a clean pair of boxers.

"Thanks," says Jackson softly. Stiles is lying on the bed, he knows Jackson can lock the door behind him.

"You're welcome." He hesitates, hating that his voice shakes. "Jackson?"

Jackson pushes the bedroom door shut, walks to the other side of the bed and slides in. "I can stay."

Stiles presses in a little closer, grateful not to be alone for just one night. He falls asleep with Jackson's arm around his chest.

* * *

Stiles smiles at Jackson once he finishes the story. He leaves out what happened the night Jackson asked Danny out. That doesn't need to be shared with anyone else.

Jackson gives him a grateful look in response.

Isaac is still snickering.

"I could tell a story about spring break freshman year," says Stiles loudly. It stops Isaac's laughter abruptly.

Isaac of course loses the ensuing argument. Stiles notices Derek's still quiet, but he's moved his chair up against Stiles' chair, and Derek's fingers keep tapping against the armrest. Stiles slides his own hand a little closer, just a brush away really, and begins the next part of his tale.

* * *

**Notes: Danny turned Jackson down and he ended up crying on Stiles' porch. Stiles took him upstairs and let Jackson cry and when Jackson kissed him, he just said "why don't you let someone actually take care of you for once" and he gave Jackson what is still the best blow job of his life (not that he'll tell Danny that) and then cuddled with him until the next morning. They never spoke of it again, but Stiles thinks it was those kind of memories that kept kanima Jackson from outright killing him back in the day.**

**Derek was thinking about Stiles' mouth. And hands. Which is completely appropriate.**

**Sometimes I like the idea of Isaac/Lydia. Today was one of those times.**

**College involved a lot of shuffling of the couples. They all opted to move past it rather than dwell on it. Their parents act confused enough for everyone.**

**I want to be clear that this is absolutely endgame Stiles/Derek and none of these other stories created any sort of relationship. Some, like Danny (and Isaac as we'll learn next) are funny. I guess I didn't want this to be complete and utter crack, (or I just don't know how to write Stiles/Jackson that way) so I want the scenes to matter, even if the story's overall point & goal is Stiles/Derek.**

**Jackson still didn't tell anyone about Mama Stilinski (who's only mention will be in this chapter because this isn't supposed to be that sad). But he did go to the hospital the day after Stiles comforted him and asked Mrs. McCall if Scott could stay at the Stilinskis' for a little while, so Stiles wasn't always there alone. When Scott showed up with sleepover gear that night, Stiles cried for an hour and told Scott everything. Jackson's never told Stiles what he did.**

**I swear this wasn't supposed to be such an emotional story. **


	3. Chapter 3

**Beginning note chapter 3: Stiles lost the rest of his virginity (Guy & girl) while staying with family the fall of his freshman year of high school. He left because he kept having panic attacks in Beacon Hills & everyone thought some separation would help. It did. **

**There might be a reference to "The First Time" in this chapter. And by might be, I mean there totally is. Also Gossip Girl & The Help.**

* * *

Stiles was not drunk. Not at all. Not even a little buzzed, in that I still have all my faculties but this Katy Perry with a techno beat music isn't making me want to kill everyone sort of way. Nope, he was stone cold sober.

He's sober by his own choice, in a show of solidarity with Isaac.

Isaac, who was coming off the tail end of the one of the worst cycles yet in the Jackson/Lydia/Isaac/Danny merry-go-round, who wanted to go out and drink and dance and in his words "fuck someone who wouldn't fuck him over in the morning". Stiles is with him to insure Isaac doesn't do anything too stupid.

"Have you found anyone to make a bad decision with yet?" asks Stiles now, leaning over to talk to Isaac.

"No. People are idiots."

"This is true. Thought you just wanted to drop that v-card though. Wasn't the whole point of tonight to no longer be holding on in hope?"

Isaac drops his head on Stiles' shoulder. "But I want it to matter. Yes, I'm a 19 year old virgin. Stupid spring break and its stupider clichés."

Stiles rubs Isaac's head and laughs when Isaac glares at him. Isaac may be a complete dick to people he doesn't know, but his glares no longer affect Stiles. Three years of werewolf drama and seven months of living together cured that. "Wanna go home?"

"Yes please," begs Isaac.

"Finally."

* * *

Stiles rolls out of bed the following morning with what feels like a hangover. And that's just supremely unfair considering the whole not drinking thing. But clearly the smoke and lights and pulsing music took a toll on his brain, because he's feeling seriously lazy. He showers and pulls on track pants and an old BHPD shirt before going into the kitchen to make coffee.

The sounds of Isaac starting his own shower prompt Stiles to make enough coffee for both of them.

Somewhere in the roommate agreement it says they're always supposed to do that, but it never happens.

Sort of like how Stiles is always dragged into relationship drama.

Isaac slouches into a chair a few minutes later. "Coffee."

Stiles shoves a cup and the caramel creamer at him. "I want tacos."

"Okay?" Isaac gives him a patented "it is too early for me to decipher your non-sequitor" look.

"Tacos are hangover food."

"You didn't drink last night."

"I still want tacos. You want to come with or stay here like a loser?"

"You're so kind. Do you take classes in how to uplift your roommate?" Isaac glares at him over the coffee.

Stiles takes away the creamer in response. "Hey, it was gonna be my treat, and I wasn't even gonna put a limit on how many tacos you can order before you have to pay for your own but if your plan is to critique my personality…"

"I'm in love with your personality," interrupts Isaac. "You are smart and kind and…"

"If you finish that with important, I will hit you."

Isaac laughs. "Whatever, buy me tacos. Let's go."

Tacos do in fact cure Stiles' faux-hangover, to the point that he's back to his normal self on the walk back to their apartment.

"So whatcha want to do today?" he asks Isaac. Stiles hopes Isaac is in the mood for movies. It's supposed to rain later and Stiles has been craving a Lord of the Rings marathon for weeks. He's finally caught up on homework too. He sips on his soda as he waits for an answer.

"Will you have sex with me?" asks Isaac.

Stiles spews Dr. Pepper all over the sidewalk. "What."

"Sex," repeats Isaac. "Will you have sex with me?"

"Like sex sex?"

"Yes. As opposed to apple sex."

"What the fuck is apple sex?"

"I don't know, I couldn't think of a better word. What the fuck do you mean sex sex?"

"Sex!" squeaks Stiles. "Normal, someone's dick is in someone else's ass sex."

"Okay then yes, that is what I meant."

They've reached the apartment and Stiles gratefully opens the door and collapses on the couch. He cracks one eye open at Isaac. "Why do you want to have sex with me? I thought you wanted it to be special."

Isaac gives him a funny look that Stiles isn't sure how to decipher. "This would be special."

"And Lydia?"

"Lydia is choosing to make other people her priority. I don't want this looming over my shoulder anymore." Isaac flops onto the couch and lays his head in Stiles' lap. "I want to have sex and you're one of my best friends and you've had a lot of sex. So I know you'd be good at it and I wouldn't regret it later."

"It's not exactly the same," says Stiles.

"I'm aware that boys and girls have different parts. I'm bi, same as you."

Stiles grins a little at him. "I meant the emotional part."

Isaac sighs. "I know. But it would still be good. Unless you don't want to."

"I didn't say that," admits Stiles. "But it wouldn't be anything more than sex for me. Don't get me wrong, this wouldn't be the first time I've thought about it…"

"That would be the day in the locker room when I forced Greenburg to give up his tickets to the rave when we tried to catch Jackson," interrupts Isaac.

Stiles gapes at him. "You knew that?"

Isaac snorts and giggles at the same time. It's kind of adorable. "Arousal was one of the first scents I picked up on. It was hard not to with Scott constantly horny for Allison."

"Okay, well while I wrap my brain around that, we're on the same page right?"

Isaac nods. "Stiles, you're probably going to replace Scott as my best friend if we keep being roommates. And you're hot. But I have literally no interest in dating you and I know you feel the same." He pauses. "I also know you haven't gotten laid in 2 months."

Stiles pushes him off the couch. "Asshole."

Isaac stays sprawled on the floor. "You know you love me."

"XOXO," returns Stiles.

Isaac flips backwards to stand up, prompting an eye-roll from Stiles. Isaac straddles Stiles' lap and looks down at him.

"So we're starting now then?" observes Stiles.

Isaac kisses him, not exactly tentative, but not in control either, like he's letting Stiles have a chance to tell him no. Stiles confirms his interest by returning the kiss, his hands tangling in Isaac's hair and pulling him closer. He licks into Isaac's mouth, tasting the lingering heat from the peppers in their breakfast food and the spearmint he ate afterwards.

When Stiles feels Isaac getting significantly more invested in the proceedings, he moves his hands down to grip Isaac's hips, rocking upwards against Isaac.

"Damn," pants Isaac. He moves back just enough to pull his shirt over his head and tugs at the hem of Stiles' tee. "Off."

Stiles grins and obeys before reaching for the waistband of Isaac's pants. He pushes them and Isaac's boxers down far enough to let Isaac's dick spring free. "Well hello," says Stiles.

"Please don't talk to my dick," huffs Isaac. He swipes his fingers over Stiles' nipples and Stiles forgets all about whatever he was going to say in response.

"Fuck you're a quick learner."

"I'm not a complete and total virgin."

Stiles rubs his thumb over the head of Isaac's dick before wrapping his hand around and pulling in steady strokes. Isaac whines & cants his hips up. "Coulda fooled me," snickers Stiles.

"Fuck you."

"Other way around." Stiles cuts off Isaac's indignant reply with another kiss. This time he twists his hand a little as he strokes. He can tell that Isaac's close, which isn't all that surprising. They are still teenagers—even he has a pretty fast recovery time—but Isaac has no experience either. He's simply reacting to Stiles' touch.

Stiles thinks Isaac looks beautiful so he says so.

"Gonna…Stiles, I need to come," breathes Isaac, resting his head against Stiles' shoulder.

"Okay," whispers Stiles and he moves his hand just the slightest bit faster.

Isaac comes with a choked off cry, slumping against Stiles. After a moment he looks at Stiles. "Um, not to be ungrateful but…" He trails off, not sure how to finish.

Stiles kisses him. "You're going to go shower and then we'll go again. By the time spring break is over, you won't be a virgin by a long shot." He pauses and snickers. "Well at least as far as guys are concerned."

"You're not funny."

Stiles shoves Isaac. "Get your naked ass off my lap, Lahey. My legs are falling asleep."

Isaac laughs. "So romantic. Will you buy me flowers when we're done?"

"Shower, dork."

Isaac is still laughing when he walks away. Stiles leans over the back of the couch to appreciate the view before getting up himself to find a washcloth and gather a few things. Spring break is starting to look up.

* * *

Some time later, happy and sated, Stiles tilts his head to look at Isaac. "You okay?"

"Yeah. Thanks."

Stiles leans over to peck Isaac's cheek. "Welcome. Now let's talk about how we're going to fix this drama you four have going on, once and for all."

* * *

Erica and Allison are both giving Isaac puzzled looks when Stiles finishes the story.

"How is that story embarrassing?" asks Allison.

"Possibly the most anti-climactic story yet," adds Erica. "And that's after Scott."

Scott throws an empty beer can at Erica. Allison attempts to hide her laughter, though it's not really working.

Isaac sighs. "It's not, I guess."

Stiles is having a difficult time focusing on the teasing amongst the pack because throughout the story, Derek's hand slowly moved over to link their fingers together. He's gently massaging Stiles' palm with his thumb now and Stiles is fast losing his ability to concentrate.

Derek does not seem to be having the same problem. "Just how many of my pack members' virginity did you take, Stiles?"

Stiles blushes. "It's not like I planned to do it. I don't have a checklist!"

"Yes, and we're all grateful for that," says Lydia, rolling her eyes at him. "He had nothing to do with my virginity. In any form."

"Hey!" snaps Stiles, momentarily indignant. "You said I was part of your first threesome."

"Fine," amends Lydia. "That doesn't actually count for anything."

"It was a threesome," corrects Stiles. "They always count."

"True," agrees Scott.

Jackson refrains from commenting on Scott's lack of experience in that area, much to everyone's unspoken pride.

"I'm surprised you and Boyd never asked anyone else to join actually," says Lydia to Erica. "You two have always been more fluid than the rest of us."

"We thought about it," admits Erica. "Even went so far as to do some research, but none of the options sounded more appealing than just the two of us."

"Research?"

Boyd gestures at Stiles. "I fucked him. He fucked me. I'm definitely straight." He thinks for a second. "Stiles was my first—and only—guy though. So I suppose you can add me to that list."

"Did you research with Stiles too, Erica?" asks Derek with a grin. His fingers are now tracing patterns on Stiles' arm.

Stiles is having a hard time believing how cool Derek is being about all this, not to mention having a near heart attack over the touching, but he's not risking losing it.

Erica shakes her head and laughs. "Nah, Stiles took my virginity back in high school during that year I took off to find myself. I researched with Allison." She high-fives Allison. "You were really freaking good with your tongue by the way. Boyd's still pretty much it for me but whoever taught you how to do that thing with your tongue has my undying respect."

Allison's giggling so hard that she can barely breathe, let alone speak, but she chokes out a "that was all Stiles" to everyone's collective shock.

Jackson says what everyone else is thinking. "What?!"

"Scott and I had a…um, difficult experience the first time he tried," begins Allison diplomatically, once she's recovered enough to explain. "So he asked if I would be upset if he asked Stiles for advice."

"You needed advice?" Lydia questions derisively.

"It's not that easy," protests Scott. "You need like a freaking schematic."

Jackson, Boyd, and Derek are all nodding their agreement, so Lydia refrains from adding another comment.

"Anyway," continues Allison. "I said that was fine but it didn't really help. And Scott, being a very sweet boyfriend, wanted to get it right. So after a very awkward conversation and I think a best out of 23 rounds of Rock Paper Scissors, we asked Stiles if he would demonstrate some techniques to Scott. In person."

"Well, you'd already had oral sex at that point so you don't get to go on the virginity list." Jackson seems weirdly pleased about that. Stiles assumes it's his competitive side poking its head up.

Allison shrugs. "Stiles was the first guy to get me to come that way."

"It counts," declares Boyd.

"Is that everyone then?" asks Stiles. "Can we now stop rehashing the fact that I'm apparently the swipe machine for every v-card in Beacon Hills?"

It's not that he's embarrassed or regretful about the sex he's had. There are a couple bad decisions back in the past but none that give him genuine regrets. But it's one thing for everyone to know the stories and it's another for all of them to come out in one evening.

Derek leans over and whispers in Stiles' ear. "So you were the first for a lot of the pack. I don't care. Can I be your last?"

Stiles jumps up from his chair so fast the thing collapses underneath him. "Derek and I have to go but you guys have fun and someone clean up and I'll see you later, okay bye."

He thinks for a brief second that he should be more embarrassed about his reaction but then Derek's behind him and sliding a hand in his back pocket as they walk to the house. Stiles stops caring about anything else.

* * *

**End notes: Wouldn't I just be the worst if I ended it there? But I won't. Because Derek and Stiles are going to have phenomenal sex and make sappy declarations about forever and worth the wait and shit like that and it will be magical.**

**I might go back one day and expand on some of the other stories that weren't fleshed out in this. But I have other WIPs that I need to finish and I want to start a "The Real Mates of Beacon Hills" AU on Tumblr. (Stiles is going to be hated at first by the other mates because he's a human [the horror!] but they all have to be nice to him because he's the Alpha's mate). It will be awesome.**

**From halfway through junior year until the summer after their freshman year in college, Lydia/Jackson/Danny/Isaac were wrapped up in a really bizarre relationship square built primarily on misunderstandings, miscommunication, and misplaced guilt. ( Basically a lot of misses for only one Miss in the whole affair). Derek and Stiles finally tag teamed over that summer break to make them realize that a simple conversation would fix the problem easy peasy.**

**Lydia and Stiles' other threesome partner was Isaac, a few months after Isaac and Lydia officially got together. It was a really good weekend.**

**Derek is cool with the stories because he already knows them all. He's the Alpha. Also his hair is full of secrets and pomade.**

**During the alpha pack time, Erica went traveling, not sure of who she was. On one of those trips, she and Stiles met up in Seattle while he was visiting colleges. They were both frustrated with a lot of things at the time and spent the weekend having sex. It was one of the stupider decisions they'd ever made and it took a few months until they were able to be friends again. But it also brought Erica home and Stiles privately thinks that the suffering was worth it to have his best girl friend back.**

**Teaching Scott how to give Allison oral was hands down the single most awkward afternoon of Stiles' entire life. It was one of the best afternoons of Allison's life. This is not something that she has ever (nor will ever) tell Scott.**


	4. Chapter 4

**Welp. That took a wee bit longer than I intended to finish (I got distracted by the super awesome plans to make an actual Neckz n Throats magazine) but it's done now. And I'm happy with it.**

* * *

Stiles isn't really sure how he made it from the middle of the yard to the hallway. It's highly possible that Derek carried him in, seeing as Stiles is currently being held up against the wall by a combined effort from Derek's hands and hip bones. Well, technically Derek's hands are mostly just groping Stiles' ass. He's pretty okay with that.

"Derek," he mumbles, pushing at Derek's chest. "What? I mean…" He shakes his head to clear the cobwebs. "Why?"

"I've been insane about you for years, Stiles," huffs Derek, breath hot against Stiles' neck. He's still licking and nipping at the skin as he speaks. It makes it very difficult for Stiles to stay on track.

"Why the fuck didn't you say anything?" He would never have let things go this long if he'd known he could have Derek like this.

Derek sucks a bruise into the hollow of Stiles' throat and Stiles keens. "You were happy at the chance for college and grad school and I couldn't leave here. I didn't want you to regret staying if I asked you. And I couldn't bear it if you left anyway."

Stiles moves his hands to cup Derek's face, tugging him up to press a much more chaste kiss than was the night's standard to his lips. "I could never regret you."

Derek grins, bright and happy and blinding at that. "I didn't want to be a reason for you to regret anything else either." He kisses him again, teeth biting at Stiles' lip, as he explores. Derek hefts Stiles up a bit in his arms as they kiss, carrying him down the hallway to his room. They separate only long enough to strip down to boxers before Stiles is scrambling on top of Derek, straddling his waist and bending down to kiss him again.

"You taste good," says Stiles, nipping at Derek's jaw. It's spicy, like the rub used on the burgers, and it makes Stiles feel like he's hot all over.

"You smell good," returns Derek. He anchors his hands on Stiles' hips and twists them so they're lying side by side.

Stiles lets himself enjoy the moment, staring into Derek's eyes as he catalogues all the colors, feeling the heat of Derek's hand on his hip, and his fingers trace mindless patterns in Derek's stubble. He wants all of Derek and yet despite the night's conversation, he thinks he could be perfectly content to stay here for now.

"Would it come out wrong if I said I don't think I want to have sex tonight?" asks Derek.

And Stiles smiles, soft and warm, because of course Derek would be feeling the same way he does. "We could just stay like this," he offers. "I like the idea of falling asleep in your arms."

Derek kisses him. "I want to wake up to your laugh. Your eyes." He kisses again and holds Stiles a little bit tighter.

Stiles wiggles until he's pressed up against Derek. "I'm not going anywhere," he whispers fondly.

* * *

In the morning, Stiles wakes up feeling more rested and content than he has in years. There were a couple short relationships at the start of college that gave him a similar feeling—though on a lesser level by far—but otherwise, he's used to awkward in the morning.

There's always that strange sensation of trying to sleep in a bed that doesn't belong to you, a pillow that won't fit your head, and waking up feeling unsettled and displaced. Then of course it's usually a matter of awkward good mornings. Because either you're happy and want to linger in the bed, or you have no idea how to exit gracefully and with minimal collateral damage.

But today is different. He's crashed in Derek's bed before—rarely with Derek in it—and he feels as comfortable as ever.

He can tell his legs are tangled with Derek's and Derek's arm is haphazardly thrown across his chest. Stiles turns his head and blinks his eyes awake. Derek's got a tiny smile on his lips, just enough of a quirk for Stiles to see it. He looks happier than Stiles has ever seen it and Stiles takes a second to be amazed that he put that there.

"Hi," he says softly.

"Hi ya back," answers Derek.

"I was afraid I dreamed this for a second."

"That I was here?" asks Stiles.

"That you stayed," clarifies Derek.

Stiles kisses the tip of Derek's nose, fond and playful. "I'm keeping you now. You'll never get rid of me."

"I'm more than okay with that," responds Derek against Stiles' lips, leaning in for a long, lingering kiss. Stiles takes advantage of the moment and licks along Derek's bottom lip, getting him to open up and let him in.

They kiss for several unhurried moments, exploring the taste of each other as their hands roam. It feels lazy, like Stiles can do this forever, because Derek's his last and that means he has all the time in the world. Derek's fingers slip under the waistband of his boxers, decidedly indicating that his interests weren't as chaste as they were last night.

Stiles is good with this development, moving his hands to tangle in Derek's hair and pull him closer.

Derek moves so he's stretched over Stiles, hand teasing the edge of Stiles' cock and lips sucking tiny marks into Stiles' neck. "Can I?" he begs.

"Anything," agrees Stiles. He's not totally sure what Derek's asking permission to do, but his answer would be the same either way.

Derek presses his knees into the bed, shifts upward to give himself room to tug Stiles' boxers down and off his legs. He pauses for a second, staring, and Stiles can't help but ask why. "Something wrong."

"You're fucking beautiful," answers Derek. He does some sort of crazy slither down the bed that has Stiles shoving a fist in his mouth to keep from moaning out loud. He plans on moaning a lot, but preferably when he's actually being touched. Just to keep any embarrassment at a minimum. Speaking of…

"I really need you to touch me," he pleads.

Derek responds beautifully, kissing the head of Stiles' dick before licking broad stripes along the underside. Stiles is painfully hard, cock leaking and while he would love to let Derek spend hours taking him apart, he needs this morning to go faster. His hands grip a little harder, not pushing but definitely indicating his desire. Derek breathes, hot and heavy, before wrapping his mouth around Stiles' cock and making Stiles' hips buck involuntarily.

It takes almost no time at all before Stiles is tugging at Derek's hair, trying to warn him to pull off.

Derek does only briefly, looks up at Stiles with eyes glinting tiny flecks of red. "If I wanted to move, I would," he says firmly, making clear his intentions. Derek does some sort of crazy growl/hum as he engulfs Stiles' dick again, causing subtle vibrations that have Stiles coming with a start and a muffled cry.

The way Derek is taking care of Stiles first is rare for Stiles. He's had good sexual partners, people who care as much about his pleasure as their own. But there still seems to always be an equal need, whereas Derek is solely focused on Stiles. He pulls off and licks Stiles clean before resting his head on Stiles' thigh. "I should have done that years ago."

Stiles had no idea he could grin so widely but he does and pulls at Derek at the same time. "C'mere and kiss me."

Derek's eyes are bright as he obliges. Stiles reaches down as Derek licks into his mouth and wraps his fingers around Derek's dick, working in steady strokes. Derek pants against him, tries to keep kissing Stiles but is mostly too focused on the sensation of Stiles' fingers—fingers he's had many a dream about over the years.

He comes with a choked out moan of "Stiles" and his body slumps over Stiles' torso, pliant and deliciously sated.

"I think we should make this our morning ritual," says Stiles when he can breathe steadily again. He kisses the top of Derek's head.

Derek mostly chooses to respond to Stiles' shoulder. "I can live with that."

A few more minutes go by before Derek lifts himself up and gets a washcloth out of the bathroom, while Stiles mentally thanks whoever wants the credit for both Derek's ass and the fact that the bathroom is attached. It bodes well for shower sex and minimal interruptions.

Derek stands at the foot of the bed on his return, gazing at Stiles, and for once Stiles doesn't feel uncomfortable. He looks his fill back for a long moment.

"Come back to bed," he says quietly.

Stiles lets himself sink back against Derek once he's cleaned them both up. He traces his fingers along Derek's arm as it curls tightly around Stiles, holding them close.

Derek isn't Stiles' first kiss, first sexual experience, first guy he's stayed overnight with, or even his first relationship. And Stiles isn't any of those things for Derek either.

But he thinks that Derek might very well be the first person Stiles has been in love with. He doesn't feel too far off the mark in thinking he's the first that Derek's truly loved. Not the ignorant love they both have felt in the past, but the kind that means you fight more because you care more and that doesn't quit during a fight anyway.

Stiles tilts his head down and kisses the tips of Derek's fingers with a small, contented noise. The truth of the matter is that firsts are fairly meaningless in the grand scheme of things. It doesn't matter where Derek comes in on the list. He's the last one. He always be.

That's all Stiles really needs.

* * *

Notes: **I honestly debated for a while as to how I wanted the sex to go and I liked this way best. I wanted it to be calm, unhurried, just about the two of them and less about sex itself. Hopefully I accomplished that.** **However, they do not only have lazy morning sex. It in fact becomes well known amongst the pack and certain nosy neighbors of Isaac & Lydia's that on certain birthdays, anniversaries, and Stiles designated "never getting out of bed" days, that a large conglomeration of adults sleep at the Martin residence (Isaac took her name when they got married) because, according to Danny "Stiles might be attractive to gay guys but it doesn't mean I want to eat breakfast in a house that reeks of sex." **  
**In Derek and Stiles' defense, they always pay for the pack to go out to a nice dinner and for get-away weekends for each couple as an apology thank you.** **The year Stiles & Derek got together, Jackson & Allison gave them a joint Christmas present. A pop-up book on how to best blow & rim Stiles. **  
**Derek glared at both of them over Stiles' laughter and threw the book away. Then he sneaked outside that night, pulled the book out of the trash, and read it six times before throwing it away again.** **Derek's contact pic for Stiles is a picture of Stiles' hand curled just right.**  
**Stiles' uses a pic of Derek's ass.** **Erica borrows Stiles' phone a lot. Isaac borrows Derek's.**


End file.
